The dramatically beautiful hills that surround Wimberley are doubly responsible for the creekside village’s charm. For while they provide a scenic backdrop and a remarkable vantage point for lovers of scenery today, they provided for decades an almost impenetrable shield from advancing civilization. The seclusion and slow progress that resulted can be largely credited for Wimberley’s “antique” small-town charm.

On April 5, 1847, at the very beginning of the pioneering push into the Hill Country, Governor Pinkney Henderson granted a patent for 1280 acres on Cypress Creek to William R. Baker. Baker soon sold his land to Jacob de Cordova, a remarkable Texas pioneer who deserves a story all to himself. Born in Jamaica to Jewish/Spanish parents, de Cordova came to Texas in 1837 and eventually acquired more than one million acres in 48 Texas counties. He was a legislator, author, editor, philosopher and promoter extraordinaire, but here he was stymied. When he couldn’t get a road put through to his new Cypress Creek property, he sold it to James Montgomery in 1856 for $1,800 ($1,000 of that amount was paid in sheep!)

During that time, the area was almost uninhabited, except for huge herds of buffalo and a wide variety of other wildlife. In 1852, one hunter named George McGehee killed 978 buffalo there, which he sold to the army at San Marcos.

Montgomery didn’t last long, either. Possibly because of a shooting incident (the story is told that he shot a man named George Blackwell in a dispute over hogs), he sold the land the very next year to William Carvin Winters, a veteran of San Jacinto who had been searching for a suitable place to build a mill. Winters built himself a home and the mill he had dreamed of; soon a small village sprang up around it. Montgomery’s name does not appear again in Wimberley history, but Winters became one of its main characters.

After losing several mills to floods along Cypress Creek, Winter ...

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